Bailey made his competitive debut at Port Vale in August 2021, though he was released at the end of the 2021–22 season following a short loan spell with Newcastle Town. He signed with Altrincham in November 2022 and was loaned out to Hanley Town and Mossley in the 2022–23 season. He joined Mossley permanently and then played for Clitheroe, Hednesford Town, Atherton Collieries, and 1874 Northwich in 2024.
Career
Port Vale
Bailey began his career at Port Vale at the age of eight and was named as Youth Player of the Year for the 2020–21 season.[4][5] He made his first-team debut on 10 August 2021, coming on as a 75th-minute substitute for James Wilson in a 2–1 defeat to Sunderland in an EFL Cup first round fixture at Vale Park.[6] He made his League Two debut as a substitute in a 2–1 defeat at Newport County on 11 December.[7] On 12 March 2022, he joined Newcastle Town of the Northern Premier League Division One West on an initial one-month loan deal; he made his debut for Castle later that day in a 2–0 home defeat to Bootle.[8] Port Vale youth teammanagerBilly Paynter said that "he played on the left of a three and was a threat, he had a very good game" and had recovered well from an ankle injury that had kept him out of action for two months earlier in the season.[9] On 19 March, he scored his first career goal with a header 12 minutes into a 2–2 draw at Mossley.[10] He played a total of nine games for Newcastle.[11] He was not offered a professional contract when his youth team contract expired in June 2022.[12]
Non-League
On 17 November 2022, Bailey signed for National League club Altrincham, immediately joining Hanley Town of the Northern Premier League Division One West on loan until the end of the 2022–23 season.[4] Altrincham manager Phil Parkinson said that he had "a real diamond on our hands".[4] He was recalled in March.[13] On 17 March, he joined Mossley on loan for the rest of the season, having scored against Mossley on his debut for Hanley.[14][15] He was released at the end of the 2022–23 season.[16] He signed with Mossley on 10 June 2023.[17] On 15 February 2024, he signed with Clitheroe.[18] Less than one month later, he joined Hednesford Town.[19] He played 12 games in the remainder of the 2023–24 season, scoring two goals, including one in the Walsall Senior Cup semi-final defeat to Chasetown.[20]
Altrincham manager Phil Parkinson has described Bailey as "a modern-day centre-forward" who can "hold the ball up, run the channels and, most importantly, score goals".[4]